Do you have to notify your brokerage which specific shares you want to sell before the sale, or can you do it afterward when filing taxes?

You need to specify which shares you want to sell at the time of the sale - you can't decide later when filing taxes. Most online brokerages have an option during the sell process where you can choose "Specific Identification" instead of FIFO (First In, First Out) or average cost. When you choose specific identification, you'll be able to select the exact lots (shares purchased on specific dates at specific prices) that you want to sell. This gives you maximum control over the tax implications of your sales and is essential for an effective homegrown dividend strategy.

For Roth IRAs, the withdrawal rules are a bit different. You can always withdraw your contributions (principal) tax and penalty free at any time. It's actually even simpler than with taxable accounts because you don't need to worry about specific identification of lots. The IRS considers withdrawals from Roth IRAs to come from contributions first, then conversions, then earnings. So you can just keep track of your total contributions over the years, and as long as your withdrawals don't exceed that amount, they're completely tax-free.

This sounds like a fantastic idea! Did you have any specific way you tracked everything? I'm worried about making it too complicated but love the real-world application.

Nothing fancy! We just use a simple chart on the refrigerator with magnets. Each kid has a section with their weekly "income" from chores, then two columns showing taxes collected and take-home pay. The family fund is a jar on the counter where the tax money goes. You definitely want to keep it simple - the point is just to visualize the concept, not create an accounting nightmare for yourself! My kids actually get excited on "budget day" when we decide how to spend the family fund. Sometimes they even vote to save it for something bigger. It's been a great lesson in collective decision-making too.

This is such a creative idea! Did you find that it made them more negative about taxes or did they see the benefits too?

Do I need to keep physical receipts for all the supplies I buy or are digital records okay? My CPA is pretty old school and I'm not sure what's actually required.

Digital records are perfectly acceptable for the IRS! I take pictures of all my receipts with my phone and organize them by month in Google Drive. Many CPAs now prefer digital because it's easier to search and organize. That said, if your CPA prefers physical copies, you might want to print them out just to make the process smoother on their end. But legally speaking, digital receipts have the same validity as paper ones as long as they clearly show the date, vendor, amount, and what was purchased.

Be careful with home office deductions though. You need a space used EXCLUSIVELY for business, not just your kitchen table where you also eat dinner. That's where a lot of people get in trouble.

Is it worth paying for the deluxe or premium versions of these tax programs? I always use the free versions but wonder if the paid ones catch more deductions?

For most simple tax situations, the free versions are perfectly adequate. The paid versions add value mainly if you have more complex situations like self-employment income, rental properties, investments, or itemized deductions. The other benefit of paid versions is better support options - some offer tax pro review or the ability to chat with a tax expert if you get stuck. But if you just have W-2 income and take the standard deduction, you're generally fine with free versions. Just make sure you're using the actual free version and not getting upsold on features you don't need.

Second this! Been using FreeTaxUSA for 3 years now. When I switched from TurboTax I actually got a BIGGER refund with FreeTaxUSA because it found an education credit TurboTax missed. Plus they don't constantly try to upsell you on stuff.

Thanks for the validation! I was worried I'd missed something since it was so much cheaper. Good to know about the education credit too - I'll have to double-check that section since I'm taking some community college classes.

Thanks for the Free File link! Do you know if they handle state taxes too or just federal? I always get confused about which services include both.

Some of the Free File partners include free state returns, but not all of them. When you go to the IRS Free File site, you can see which providers offer free state filing along with federal. It varies by state too - some states have their own free filing programs separate from the federal Free File program. I'd recommend checking the specific provider details when the program opens in January. The IRS usually has a tool that helps you find which Free File option is best for your situation, and it will show whether state filing is included or not.

Great idea with the calendar reminders! Does anyone know if there's some kind of email alert system from the IRS where they notify you when filing season begins?